Acetone → 3-(1H-imidazol-4-yl)-2-isopropylamino-propionic acid

HRID 1611803Notes

Reaction equation

HRID 1611803 reaction equation
[NH2:1][C@H:2]([C:9]([OH:11])=[O:10])[CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1.[CH3:12][C:13]([CH3:15])=O.[H][H]>C(O)C.[Pd]>[NH:6]1[CH:5]=[C:4]([CH2:3][CH:2]([NH:1][CH:13]([CH3:15])[CH3:12])[C:9]([OH:11])=[O:10])[N:8]=[CH:7]1

Participants

6

Reactant 3

HCID 180AcetoneHCID 178418361HCID 178418361, compound2×HCID 178419078HCID 178419078, compound

Product 1

HCID 1784571393-(1H-imidazol-4-yl)-2-isopropylamino-propionic acidYield 37.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of L-histidine (15.51 g, 100 mmol) and acetone (14.7 mL, 200 mmol) was agitated in an atmosphere of hydrogen (pressure, 46-51 psi) at 40° C. in 500 mL ethanol in the presence of Pd/C (20%, 2 g) until the absorption of hydrogen had ceased. The mixture was filtered, and the filtrate was concentrated to dryness under reduced pressure. The white solid thus obtained was triturated with ethanol and dried under vacuum to give 7.31 g (37%) of the title compound as a white solid.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness under reduced pressure
  3. customThe white solid thus obtained
  4. customwas triturated with ethanol
  5. customdried under vacuum

Sources & evidence

ORD record
ord-5478e6e00eac45aba273091acfebc6c7
Source dataset
uspto-grants-2006_01
Patent number
US06989448B2

Reaction notes

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